I gave bookmaker a hard time last week when they insisted on charging me for a withdrawal, so I figure that I at least owe them a somewhat positive report for getting the check to me sooner than I expected. Even though I requested the payout past their cut-off time last Tuesday, the check arrived within a week.

Ok, I know this topic has been discussed thoroughly but this seems like a catch 22 situation for these two guys on sportsbook.com. If they are from the U.S., and if they win, do they pay the taxes and risk arrest for online gambling or, do they not report it and risk arrest for tax fraud? This is not like winning a couple of hundred bucks gambling online. This is getting into big money.

Anyone who is playing SB's online from the USA is not paying any taxes, legal or illegal, since it's not legal to bet online.As someone else said, continue to make withdraws until you get your money out. It might take a long time, but continue to do so. I'm not sure if SB dot com allows transfers to other books, so that's might be an option also.

I've been so busy lately, but I hit some major parlays last week for a dime, so it was all good. I also took a few units on KC @ -3.

This is an example of some of the parlays I hit. I had some RRs on a few teams also, and in some other smaller parlays I bought up with Auburn -2/-3, which helped the payouts. It would have been all for naught if NE would have lost. Wager Type : Parlay (8 team)Wager Status : WinRisk / To Win Amount : 10.00 / 177.20(USD)Accepted : 12/7/2013 10:55AM - PST

I'll probably add the Broncos ML to one of my open parlays or buy it down to -3 or -6.

Line is dropping. It's 10 at some books now, and seeing it -10 (-103), which is the best line I can find.

I'll be taking the over 65.5 for the FSU/Auburn game.Auburn doesn't play much defense and FSU can light it up. It could easily be similar to the last game Auburn played.BM has the Auburn at +9.5 -110. I'd love taking it if I can get it at +10.

I'll probably add the Broncos ML to one of my open parlays or buy it down to -3 or -6.

Line is dropping. It's 10 at some books now, and seeing it -10 (-103), which is the best line I can find.

I'll be taking the over 65.5 for the FSU/Auburn game.Auburn doesn't play much defense and FSU can light it up. It could easily be similar to the last game Auburn played.BM has the Auburn at +9.5 -110. I'd love taking it if I can get it at +10.

All I will say is be very careful betting bowl games early when they are a month away from being played. A lot can happen.

Yes, but I believe you owe the taxes on the full amount in the year that you win it. If a person were to get audited, would the IRS just take the info that you provided on the amount you won or would they want something official from sportsbook? And with sportsbook being offshore, they don't have to report anything.

At a casino, yes, you are right. If you go to Shreveport and win $10k playing cards, they will hold out taxes when they give you your winnings. But, you can claim gambling losses up to the amount you claim gambling winnings. You are 100% right about the off shore books. They aren't under US jurisdiction and tax laws. The problem is going to be explaining why you have a $10k check to cash. That's why I would request a $7k-$8k check every month until is paid out.

The way I see it, until I can't pay a bill, or my kids go without Christmas, it's still a hobby. lol.

At a casino, yes, you are right. If you go to Shreveport and win $10k playing cards, they will hold out taxes when they give you your winnings. But, you can claim gambling losses up to the amount you claim gambling winnings. You are 100% right about the off shore books. They aren't under US jurisdiction and tax laws. The problem is going to be explaining why you have a $10k check to cash. That's why I would request a $7k-$8k check every month until is paid out.

Actually I'm not sure that's correct. I have won well over 10k several times playing blackjack at a casino. Every time it has been marathon sessions. You are not winning that 10k on one bet. I have never paid taxes or had to. Now at the horse track if you bet say 50.00 and hit a trifecta that pays over like 799.00 or something you have to pay taxes.

Blackjack maybe you are playing 25.00 50.00 100.00 or so a hand. It's cumulative and therefore shouldn't fall under that bracket. A one time sports wager however that pays those amounts I think is different.

Actually I'm not sure that's correct. I have won well over 10k several times playing blackjack at a casino. Every time it has been marathon sessions. You are not winning that 10k on one bet. I have never paid taxes or had to. Now at the horse track if you bet say 50.00 and hit a trifecta that pays over like 799.00 or something you have to pay taxes.

Blackjack maybe you are playing 25.00 50.00 100.00 or so a hand. It's cumulative and therefore shouldn't fall under that bracket. A one time sports wager however that pays those amounts I think is different.

I could easily be confused, but now that I think of it, I've never had to pay taxes on my Poker winnings either. The reason I said that is that I know if you win a certain amount on a slot machine, you have to pay taxes on it, especially if it's a jackpot. There's probably a limit where you do have to pay taxes if it's over a certain amount, and don't beneath that.

Logged

McHogLovin

I could easily be confused, but now that I think of it, I've never had to pay taxes on my Poker winnings either. The reason I said that is that I know if you win a certain amount on a slot machine, you have to pay taxes on it, especially if it's a jackpot. There's probably a limit where you do have to pay taxes if it's over a certain amount, and don't beneath that.

Local Cherokee Casino you have to claim poker winnings over 2500. But if you win 12k you just have your poker buddies go to the cage with ya and cash out 2k 6 times and go home.

It is confusing to me as well...one of my friends once hit 10k on a penny slot in Vegas and didn't have to pay a dime in taxes. They just counted out the cash and said have a nice day. I really don't understand how it all works.

Another buddy of mine...at a different casino got hot on the roulette wheel...won about 8k after buying in for 500 and they tried to make him fill out a form/pay taxes. If I remember right he had different people cash in 1k-2k at a time avoid it.

Once at the horse track I hit a $500 bet for about 6k and didn't have to pay a dime in taxes...but I have seen people who hit a trifecta for $700 who had to pay taxes. Lol like I said I don't get all this stuff.

You're supposed to get taxed on gambling winnings. You should receive a W2-G from the casino around tax time that reports all winnings and with holdings. If you didn't with hold at the window you will on your tax return.

You're supposed to get taxed on gambling winnings. You should receive a W2-G from the casino around tax time that reports all winnings and with holdings. If you didn't with hold at the window you will on your tax return.

Dude. If you play blackjack for 30 hours then walk over to the cage and cash in 14 grand in chips you don't pay taxes on it. I never have. Have never received anything from the casino or the irs. It's different hitting a jackpot on a slot. On those you will pay taxes.

you pay federal taxes on any one bet that pays 600-1 or higher...amount won does not matter ie if you bet $10,000 and win $10,000, its tax free. Bet $1 and win $600 (or more) will result in them holding 25% (i think that's still the % withholding).

Dude. If you play blackjack for 30 hours then walk over to the cage and cash in 14 grand in chips you don't pay taxes on it. I never have. Have never received anything from the casino or the irs. It's different hitting a jackpot on a slot. On those you will pay taxes.

If your winnings, regardless of where they came from, are subject to federal with holding you will receive a WG-2. If it isn't subject to federal with holdings you still are supposed to report it as income which can result in a lower refund or having to pay more in with your tax return.

you pay federal taxes on any one bet that pays 600-1 or higher...amount won does not matter ie if you bet $10,000 and win $10,000, its tax free. Bet $1 and win $600 (or more) will result in them holding 25% (i think that's still the % withholding).

Thanks for the info but I'm still trying to find out what a person, like these two guys that bet on Auburn on Sportsbook, would do If he were to win a large amount online whether it be at one time or over the season(s). From what I understand, any income is taxed no matter how you made it. Now I know if you win at a casino and they pay you in cash that you are not going to report it unless you know the casino is reporting it. My question is more for online offshore winnings. How do you handle it when (if) you get audited and you have several thousand in deposits from checks from your offshore acct. If you listed it as income on your tax return, then you are possibly ok with IRS but would they turn you over to the feds if you told them where it came from thus getting in trouble for wagering. If you don't list it then you are in trouble for tax evasion, thus The catch 22 for which I am looking for an answer. If you don't ever get audited or never have the bank file a suspicious activity report (SAR) on your check, then you are ok. But if you ever do, then you have to come up with an answer.

Thanks for the info but I'm still trying to find out what a person, like these two guys that bet on Auburn on Sportsbook, would do If he were to win a large amount online whether it be at one time or over the season(s). From what I understand, any income is taxed no matter how you made it. Now I know if you win at a casino and they pay you in cash that you are not going to report it unless you know the casino is reporting it. My question is more for online offshore winnings. How do you handle it when (if) you get audited and you have several thousand in deposits from checks from your offshore acct. If you listed it as income on your tax return, then you are possibly ok with IRS but would they turn you over to the feds if you told them where it came from thus getting in trouble for wagering. If you don't list it then you are in trouble for tax evasion, thus The catch 22 for which I am looking for an answer. If you don't ever get audited or never have the bank file a suspicious activity report (SAR) on your check, then you are ok. But if you ever do, then you have to come up with an answer.

Honestly I don't know. Two years ago I hit a ten team parlay online. Bet 5.00 and it paid out like 3600.00. I just made the withdrawal. I would imagine 100k would draw quite a bit more attention though!

Thanks for the info but I'm still trying to find out what a person, like these two guys that bet on Auburn on Sportsbook, would do If he were to win a large amount online whether it be at one time or over the season(s). From what I understand, any income is taxed no matter how you made it. Now I know if you win at a casino and they pay you in cash that you are not going to report it unless you know the casino is reporting it. My question is more for online offshore winnings. How do you handle it when (if) you get audited and you have several thousand in deposits from checks from your offshore acct. If you listed it as income on your tax return, then you are possibly ok with IRS but would they turn you over to the feds if you told them where it came from thus getting in trouble for wagering. If you don't list it then you are in trouble for tax evasion, thus The catch 22 for which I am looking for an answer. If you don't ever get audited or never have the bank file a suspicious activity report (SAR) on your check, then you are ok. But if you ever do, then you have to come up with an answer.

If these guys hit their Auburn tickets they will most definitely need to consult a CPA.

Hey DadVader, are you going to use your spreadsheet data to play the bowl games?

Thanks for posting.

Definitely. I've been immersed in handling a family emergency, so football dropped off my radar for the last week or so. The emergency is over, and the outcome was what I had hoped for and expected (which is a HUGE relief). It will take me a few days to get back up to speed on bowl season, but I'll run the numbers and post what I find.

Definitely. I've been immersed in handling a family emergency, so football dropped off my radar for the last week or so. The emergency is over, and the outcome was what I had hoped for and expected (which is a HUGE relief). It will take me a few days to get back up to speed on bowl season, but I'll run the numbers and post what I find.